Herbicidal composition



Patented Apr. 7, 1953 HERBICIDAL cc PQsITION David T. Mommy and Arthur H. Schlesinger, Days ton, ,Ohio, assignors to Monsanto Chemical Com any S -LouisM acc m'atioh aim e- No Drawing.

p 1 The p-resent-inyention provides new. and highly valuableherbicidal compositions and methods. of destroying .or preventing plant. growth in which such jlcompositions are employed.

We have found that improved, very .efiicient herbicidal compositions areobtained when there are prepared .oileinewater emulsions f cyano ether testers haying the, formula I B u m --cai=-c..c.octh than i wh c :lt,.R.'....:R"* a dit arc selected fro the class consisting of hydrogen and the methyl radical and n is an integer of from 1 to 3.

Gompounds having the above formula form the subject of the 'copending application of David T1 Mowry and Eugene L. Bingwa'ld, Serial No. 262,157, filed of even date. They are ob,- tainable by contacting, in the presence of an esterifying agent, acrylic acid or an acid halide thereof renas acryl'yl .chloride .or :methacrylyl bromide with a hydroxy alkoxy nitrile having the formula MB/I m septa n which R,- R23 and :R, are as d fihedabq a. H droxy alkoxy nitrilcs. ha in this formula are easily obtainable-by thc add ion of acrylic. ile or mcthaicry nitrile to alhy cne. ely c s. r to. pclya11sylchcglycolsharmshe form la copolymerized with vinyl chloride to yield the Application December 11,1951, Serial No. 262,158

6 Claims. (01. 1115s,

present synthetic. rubbers. are; e o-emetic.

oxylethyl acrylate. or .mcthacrylate which 9b. tainable from acrylic: acid. or in tha rylic acid a d 2-('.2-hydroxyc.thc.xy ht pioh tril cyanop topoxyiethyl acrylatc r mcthacty ai which isobtainable from cr lic a id or new acrylic acid and..z-fiz-hyclmxycth x l-l:mcth l-- propionitrile; 2-i -z c a ccth xw hcxylethyl acrylat chmcthacryla c which s obtai ab e from acr l c ac d. or mcthac ylic acid a 2 [2 2ehydrcx eihoxwcthms lp o io trile; z -lz-cy mc th xw lemc hy c hy c fy t P hcthacrxlate which obta able f m ac y ic or methacrylic acid and 2-(2-hydroxyprop'ogy). propionitrile, etc.

Herbicidally active emulsions of the present cyano ether esters may be obtainedby first dis.- solving the esters in an organic material which is a solvent therefor and then mixing the organic solution with water in the presence of an emulsifying agent. Because of the high toxicity of thepresent cyano ether esters against 7 g plants and the efficiency with which organic solutions of the same may be dispersed in an aqueous vehicle, extremely good herbicidal properties are evidenced by havinglonly very small concentrations of the'ester, for example, concentrations of from 0.1 per cent to 2 per cent by weight of the total weightofjthe emulsion.

. Emulsi ying agents which be em lo a e. t se customarily use the a t for the p eparation of chem-water emulsions, ca, io ic .1" no c emulsif ing r di pe in gen uch a h lcns-cha n alky en hcsu f n s o polyglycol ethers. The emulsifying agents are likew e emp oyed n only v ry m 1 n ent a ion say, j'a u n i y Q f m 0.0. 1 l Or cent by weight of the total weight of the emul sion, and hence do not affectgthe chemical stability of'tlie acrylate.

The emulsions'may'be used to destroy already existing plant growth bykiirect application to the undesirable plants, e. g, by spraying; or the emulsions maybe employed to prevent plantrowth by application to media which-normally support plant'- growth. When employed topre vent plant growth for example inparkingareas; highway abut-ments, railway yards 9136;, the emulsions' may be applied by spraying only the sur,-.. face of said media or they may be admixed w-ith said media. Generally; spraying of only the soil. surfaces is'sufficient' to prevent plant growth in,

areas which are to be keptclear of'p'lants. Hows-.1

ever the emulsions may be incorporated: into;

terials, e. g., oils, cinders, etc. i

The present invention is further illustrated, but not limited by the following examples:

Example 1 each of the acrylates based on the total weight v of each emulsion. The quantity of emulsifying agent used was 0.2 per cent by weight, based on the weight of each emulsion.- Said emulsifying agent comprised a mixture of a polyalkyleneglycol derivative and an alkylbenzenesulfonate.

Three-week old corn and bean plants were sprayed with the respective emulsions, two plants of each variety being employed. The spraying was continued until droplets formed on and/or fell from the foliage and stems of the sprayed plants, up to 15 ml. of the aqueous suspension being applied to each plant. The sprayed plants as well as two untreated blank specimens of each plant were then allowed to remain under standard conditions of sunlight and watering for a period of one week. At the end of that time the sprayed plants were compared with the untreated plants in order to determine the extent of injury, if any. The following observations were made.

Another method of testing for herbicidal efficiency of a chemical involves noting the effects on seed germination and plant growth which may be evidenced by spraying soil surfaces. This test, commonly known as a pre-emergence test was conducted as follows:

Boxes having a 5" x 5" exposed area were partially filled with a layer of soil and seeds were placed thereon and then covered with a to /g" layer of soil which had been screened to V sieve. Test boxes containing 20 seeds each of cucumber, beet, radish and rye grass seeds, respectively, were prepared. The surface soil of the seeded boxes was then sprayed, respectively, with the 0.3 per cent and 1.0 per cent emulsions of 2-(2-cyanoethoxy) ethyl acrylate described in Example 1. The quantity of each emulsion which was applied was calculated to correspond to either 20 lbs. of the 2-(2-cyanoethoxy) ethyl acrylate per acre or to 50 lbs. per acre. In the present instance 10.8 cc. of the 0.3 per cent emulsion per square inches of surface soil was calculated to correspond to 20 lbs. of the chemical per acre and 9.1 cc. of the 1.0 per cent emulsion to 50 lbs. of the chemical per acre. The sprayed boxes as well as similar seeded but unsprayed 7 test boxes were then maintained at standard conditions of temperature and watering for a period of two weeks. At the end of that time the number of healthy seedlings in each box was counted. Thus the number of non-emerging and damaged seedlings was obtained by difference. This difference is designated as X. Per cent phytotoxicity of the herbicidal composition was determined by the ratio of X to the number of healthy seedlings.

There was evidenced from 71 per cent to per cent phytotoxicity to all four of the tested varieties at the 50 lbs/acre rate of application and a phytotoxicity of from 46 to 70 per cent to radish and rye grass at the 20 lbs/acre rate. The phytotoxicity to cucumber and beets at the 20 lbs/acre rate was less marked.

Example 3 The herbicidal activity of 2-(2-cyanoethoxy) ethyl acrylate was determined by germination of cucumber seeds, for 4 days at a temperature of 76 F. in the presence of an aqueous emulsion of the acrylate at aconcentration of 100-p. p. m. Fifty seeds were used for each of two duplicate tests. The results were expressed as per cent length of the primary roots in the presence of the chemical as compared with the length of the primary roots of controls which had been germinated in water. The activity of a number of related compounds as obtained by the same testing procedure are included for comparison.

The following results were obtained.

While the present esters are most advantageously used as herbicides when incorporated into oil-in-water emulsions, they may also be used in other plant destroying methods. Thus they may be mixed with solid carriers such as clay, talc, pumice and bentonite to give herbicidal compositions which may be applied in toxic quantitles to undesired plant growth. The present esters may also be mixed with liquid or solid agricultural pesticides, e. g., insecticides and/or fungicides. Although solutions of the cyano ether esters in organic solvents therefor may be employed as herbicidal compositions, we have found that the oil-in-water emulsions of the present acrylates possess an improved tendency to adhere to plant foliage, and that the emulsions require less of the esters to give comparable herbicidal efiiciency than do the organic solutions or the dry mixtures.

What we claim is:

1. A herbicidal composition comprising an oilin-water emulsion of a cyano ethyl ester having the formula in which Y, R, R, R" and R are selected from the class consisting of hydrogen and the methyl radical and n is an integer of from 1 to 3, said cyano ethyl ester being present in said emulsion in a quantity which is toxic to plant growth.

in-water emulsion of 2-(2-cyanopropoxy) ethyl acrylate, said acrylate being present in said emulsion in a quantity which is toxic to plant growth.

4. The method of destroying undesirable plants which comprises applying to said plants a toxic quantity of a herbicidal composition comprising an oil-in-water empulsion of a cyano ether ester having the formula RI! R!!! alaoinfi a e 6 in which Y, R, R, R" and 'R' are selected from the class consisting of hydrogen and the methyl radical and n is an integer of from 1 to 3.

5. The method of destroying undesirable plant growth which comprises applying to said plants a toxic quantity of a herbicidal composition comprising an 'oil-in-wa'ter emulsion of 2-(2-eyanoethoxy)ethyl acrylate.

6. The method of destroying undesirable plant growth which comprises applying to said plants a toxic quantity of a herbicidal composition com-Q prising an oil-in-water emulsion of 2-(2-cyano g No references cited. 

4. THE METHOD OF DESTROYING UNDESIRABLE PLANTS WHICH COMPRISES APPLYING TO SAID PLANTS A TOXIC QUANTITY OF A HERBICIDAL COMPOSITION COMPRISING AN OIL-IN-WATER EMPULSION OF A CYANO ETHER ESTER HAVING THE FORMULA 